Amides of n-beta-hydroxyalkyl amino carboxylic acids and process of preparing same



Patented Sept. 13, 1934 All!!!) E S OF N BETA HYDROXYALKYL AIVHNO CABBOXYLIC AEIDS AN'D ?BOC ESS F PREPARING SAW Heinrich Ulrich and Karl Saurwein, Ludwlgshafen-on-the-Rhine, Germany, assienors to l. G. Farbenindustrie Akiiengesellschait, Frankiort-on-the-Main, Germany No Drawing. Application February 6, 1932, Serial No. 591,451. in Germany February M3, 1931 13 Claims.

The present invention relates to the production of assistants for the textile and related industries.

We have found that valuable assistants for the textile and related industries, such as wetting, washing, dispersing, softening and like agents, can be obtained by causing N-fi-hydroxyalkyl amino carboxylic acids containing a hydrogen atom connected to the nitrogen atom to react with halides of aliphatic carboxylic acids containing at least a carbon atoms. The said fatty acid halides may be chosen from the halides of open chain or cycle-aliphatic carboxylic acids especially of those of natural fatty acids and particularly of those of vegetal, i. e. animal and vegetable, origin, such as butyric, lauric, palmitic, stearic, oleic, montanic, myristic and like acids as well as of halides from mixtures of such acids, as for example those of the acids of coconot or peanut oils, train oils and like natural acids. Halides of the acids from the oxidation of paraffin waxand naphthenic .acids may be also employed as well as halides of halogenated acids of the said nature as for example of dichlor stearic or mono-chlor palmitic acids. In

most cases the chlorides of the acids will be employed, since they are easily available in comparison to bromides. The said N-p-hydroxyalkyl amino carbonylic acids correspond to the general formula CHg-CH(OH)X in which X denotes hydrogen or an alkyl radicle, such as methyl, ethyl, propyl, butyl, amyl or higher alkyl radicles. These carboxylic acids can he obtained for example by saponifying nitriles obtainable according to the present inventors application for U. S. Patent Ser. No. 591,450 filed February 6th, 1932 by condensing hydrocyanic acid with oxazolidines corresponding to the general formula the presence of a quantity of alkali sumcient to neutralize the halogen hydride formed, the alkali, such as sodium or potassium hydroxides or carbonates or calcium hydroxide, being usually employed in the form of their aqueous solutions. The reaction is preferably carried out at temperatures between 0 and 80 C., the temperature varying with the activity of the. initial materials and being raised, if the reaction is to be accelerated. For attaining a most uniform reaction the acidhalide is preferably introduced, while stirring, into an aqueous solution of the alkali metal salts of the amino carboxylic acids. The products obtained. according to the present invention are apparently amides oi the amino carboxylic acids and fatty acids and correspond to the general formula v oin-omomx RC 0-N o x x c cor 7 in which R denotes an aliphatic radicle containing atleast 3 carbon atoms, X denotes either hydrogen or an aliphatic radicle and Y denotes hydrogen or a radicle of a base such as Na or K; thus R-CO may be the radicle of butyric, capryllc, lauric, oleic, stearic, di-chlorstearic, palmitic, mono-chlorpalmitic, montanic or like acids as described above, especially of those which contain from 4 to 20 carbon atoms, while X corresponds to the corresponding radicles of the original hydroxy-alkyl amino carboxylic acids. By the addition of alkili and the formation of halogen hydride, alkali halides are formed as by-products which may be left in the reaction products without impairing their properties or may be removed in any usual and convenient manner.

By the process according to this invention products are frequently obtained which are soluble in water and which are eminently suitable as wetting, washing, dispersing and softening agents in the textile industry; they may be employed in acid, neutral and alkaline treatment baths without any deposits of dimcultly soluble salts even when using water containing lime. The said condensation products may be employed with special advantage in the parchmentizing or mercerizing h'eatment of cotton fabrics or of paper with concentrated sulphuric acid; most of them, especially those prepared from acid halides with'from 8 to about 14 carbon atoms, easily dissolveior example in sulphuric acid of' 5 B. as is usually employed for the parchmentizing of paper. By adding-from 0.5 to 10 per cent by weight of the substances to the sulphuric acid, the goods to be treated are wetted very rapidly and uniformly so that a previous wetting is unnecessary. From 1 to 5 grams of the said substances may be added to each litre of a bath for rendering artificial silk smooth and soft. The said products are also suitable as dispers ing agents for dyestuffs, resins, waxes, paraffln oils or waxes, mineral or vegetable oils or fats and organic solvents in liquids in which the said materials are more or less insoluble.

The condensation products may be used as such or together with other substances, such as soaps, Turkey red oils or dispersive sulphuric esters of other aliphatic compounds or 'sulphonic acids of aromatic compounds, or with salts, such as perborates, Glaubers salt or tartaric acid salts or with glue, gum arabic or dextrine, a highly efiicient composition consisting for example of N- hydroxyethyl glycocoll stearic amide mixed with the sulphuric ester of mono-ethanol amine coco fatty acid amide. The employment of the said condensation products in conjunction with organic solvents, such as cyclohexanol, tetrahydronaphthalene, water-insoluble liquid or solid alcohols or ketones, is also advantageous.

The following examples will further illustrate the nature of this invention but the invention is not restricted to these examples.

Example 1 One molecular proportion of the hydroxy ethyl amino acetonitrile obtainable according to the aforesaid application Ser. No. 591,450 from molecular proportions each of mono-ethanol amine, formaldehyde and hydrocyanic acid'is saponified by boiling with 2 molecular proportions of caustic soda in the form of a 20 per cent aqueous-solution until the whole ammonia formed by the saponification is driven 011. 1 molecular proportion of coconut oil acid chloride is dropped at from 20 to 30 C. into the alkaline solution obtained. A water-soluble oily, neutral solution of the sodium salt of the amide and sodium chloride is formed which is readily soluble in alkalies of any concentration and which has a very good wetting power. The product is also soluble in strong mineral acids; for example 0.5 to 1 per cent thereof may be introduced into sulphuric acid of about 54 B., its good wetting action not being impaired thereby. The coconut oil acid chloride may also be replaced by stearic chloride, a water-soluble paste being thus obtained, the product consisting then mainly of the amide obtainable by condensing coconut oil fatty acid chloride with amino-ethanol sulphuric ester with 1 part of the aforesaid product be added to each litre of an aqueous bath for the treatment of artificial silk a very smooth and soft silk is obtained.

Example 2 The a- (n-propyl) -a (N-p hydroxyethyl amino) acetonltrile cnrcmon HN\ /CN CH obtainable according to the aforesaid application for patent Ser. No. 591,450 from equimolecular proportions of mono-ethanol amine, butylaldehyde and hydrocyanic acid, is saponified as described in Example 1. 1 molecular proportion of the product obtained is caused to react with 1 molecular proportion of n-butyric chloride. The reaction product is a water-soluble oil which has a very good wetting power in neutral and alkaline baths, as for example in caustic mercerizing lyes, as well as in sulphuric acid of from 40 to 70 per cent strength; the free acidmay be obtained by acidifying the aforesaid product for example with hydrochloric or sulphuric acids.

Example 3 The carboxylic acid HN-CHr-CHaOH coon obtainable by saponifying the nitrile obtainable according to the aforesaid application Ser. No. 591,450 from mono-ethanol amine, methyl-isono propyl ketone and hydrocyanic acid is condensed with the equimolecular amount of stearic chloride.

The paste obtained is dried on the water-bath,

a water-soluble powder is thus obtained which is an excellent washing agent. 5

What we claim is:-

1. The process for the production of amides suitable as assistants for the textile and related industries which comprises reacting a N-s-hy-' droxyalkyl amino carboxylic acid containing a hydrogen atom connected to the nitrogen atom with a halide of an aliphatic carboxylic acid containing at least 4 carbonatoms.

2. The process for the production of amides suitable as assistants for the textile and related industries which comprises reacting a N-s-hydroxyalkyl amino carboxylic acid containing a hydrogen atom connected to the nitrogen atom with a halide of an aliphatic carboxylic acid containing at least 4 carbon atoms in the presence of a quantity of aqueous alkali equivalent to that of the said halide.

3. The process for the production of amides suitable as assistants for the textile and related industries which comprises reacting a N-fi-hydroxyalkyl amino carboxylic acid containing a hydrogen atom connected to the nitrogen atom with a halide of an aliphatic carboxylic acid containing at least 4 carbon atoms at a temperature between 0 and C. in the presence of a quantity of aqueous alkali equivalent to that of the said halide.

4. The process for the production of amides suitable as assistants for the textile and related industries which comprises reacting a N-p-hydroxyalkyl amino carboxylic acid containing a hydrogen atom connected to the nitrogen atom with a halide of a fatty acid containing from 4 to 20 carbon atoms at a temperature between 0. and 80 C. in the presence of a quantity of aqueous alkali equivalent to that of the said halide.

-5. The process for the production of amides suitable as assistants for the textile and related industries which comprises reacting a N-fi-hyc droxyalkyl amino carboxylic acid containing a hydrogen atom connected to the nitrogen atom with a halide of a fatty acid mixture obtainable from vegetal material, at a temperature between 0 and 80 C. in the presence of a quantity of aqueous alkali equivalent to that of the said halide.

6. Condensation products suitable as assistants for the textile and related industries comprising amides corresponding to the formula om-cmomx n-o O-N c x (x)-0ooY in which R denotes an aliphatic radicle containing at least 3 carbon atoms, X denotes either hydrogen or an aliphatic radicle and Y denotes hydrogen or an alkali metal.

'7. Condensation products suitable as assistants for the textile and related industries comprising amides corresponding to the formula clan-onion n-c 0N o x X 0 OY in which R denotes an aliphatic radicle containing at least 3 carbon atoms, X denotes either hydrogen or an aliphatic radicle and Y denotes hydrogen or an alkali metal.

8. Condensation products suitable as assistants for the textile and related industries comprising amides corresponding to the formula CHr-CH(OH)X 1 c x x o0oY v in which R denotes an aliphatic radicle containing from 3 to 19 carbon atoms, X denotes either hydrogen or an aliphatic radicle and Y denotes hydrogen or an alkali metal.

9. Condensation products suitable as assistants lor the textile and related industries comprising amides corresponding to the formula v era-onion ing from 3 to 19 carbon atoms, X denotes either.

hydrogen or an aliphatic radicle and Y denotes hydrogen or an alkali metal. I

p 10. Condensation products suitable as assistants Ior the textile and related industries comprising amides corresponding to the formula UHF-CHICK a-o 0-N era-co OY in which R denotes an aliphatic radicle containing from 3 to 19 carbon atoms and Y denotes hydrogen or an alkali metal.

11. Amides, suitable as assistants for the textile and related industries, corresponding to the formula oHr-cmomx n-o O-N o x x -coor om-omon cum-c041 era-coon 13. A condensation product, suitable as assistant for the textile and related industries, comprising the amide oi' N-hydroxy-ethyl glycocoll and acids 01' coconut oil which corresponds to the formula cm-oraoir CHI-000E in which n-co denotes the radicle oi. the acids ofcoconut' oil.

- HEINRICH ULRICH.

KARL SAURWEIN.

in which n denotes an aliphatic radicle contain- 

